Hydrochloric Acid → HCID 178485664, compound

HRID 2257009Notes

Reaction equation

HRID 2257009 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH:13]=[CH:14][C:15]([N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:16])=[C:9]([O:25]C)[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](/[CH:13]=[CH:14]/[C:15]([N:17]([CH3:18])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:9]([OH:25])[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 54232957HCID 54232957, compound

Product 1

HCID 178485664HCID 178485664, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Chloro-4-[2-(phenyl-N-methylaminocarbonyl)ethenyl]-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.150 g) was suspended in methylene chloride (10 mL) under nitrogen. This suspension was treated in one portion with boron tribromide (285 mg, 1.07 μL) via syringe at ambient temperature. The mixture immediately went from a buff suspension to a rust red mixture. Stirring was continued for one hour. The mixture was then treated with saturated aqueous sodium bicarbonate (10 mL) and the pH of the mixture was then adjusted to pH 3 with concentrated hydrochloric acid and the resulting buff colored suspension was stirred for an additional hour. The solid product was filtered off and washed with cold water and dried. The crude product was dissolved in warm ethyl acetate (15 mL) and hexane was added gradually to precipitate the product. The product was filtered off and dried under vaccum to afford the desired product 84 mg. Yield 58%; 1H NMR (d6 -DMSO) 7.63 (d,1, J=16), 6.80 (d,1, J=16) trans olefin protons; MS: m/z=383 (M+1). Analysis for C20H15ClN2O4 : Calculated: C, 62.75; H, 3.95; N, 7.32; Found: C, 62.45; H, 3.94; N, 7.08.

Workup

  1. stirringthe resulting buff colored suspension was stirred for an additional hour
  2. filtrationThe solid product was filtered off
  3. washwashed with cold water
  4. customdried
  5. dissolutionThe crude product was dissolved in warm ethyl acetate (15 mL)
  6. additionhexane was added gradually
  7. customto precipitate the product
  8. filtrationThe product was filtered off
  9. customdried under vaccum

Sources & evidence

ORD record
ord-9d9de35a7e26421cbc45c1c13d4e1896
Source dataset
uspto-grants-1997_08
Patent number
US05656626

Reaction notes

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